JP2646421B2 - Obesity prevention agent - Google Patents

Obesity prevention agent

Info

Publication number
JP2646421B2
JP2646421B2 JP5278992A JP27899293A JP2646421B2 JP 2646421 B2 JP2646421 B2 JP 2646421B2 JP 5278992 A JP5278992 A JP 5278992A JP 27899293 A JP27899293 A JP 27899293A JP 2646421 B2 JP2646421 B2 JP 2646421B2
Authority
JP
Japan
Prior art keywords
glycolipid
fraction
oil
ethanol
obesity
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
JP5278992A
Other languages
Japanese (ja)
Other versions
JPH07107939A (en
Inventor
弘幸 竹内
春気 溝渕
建夫 無類井
久直 竹内
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
NITSUSHIN SEIYU KK
Original Assignee
NITSUSHIN SEIYU KK
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by NITSUSHIN SEIYU KK filed Critical NITSUSHIN SEIYU KK
Priority to JP5278992A priority Critical patent/JP2646421B2/en
Publication of JPH07107939A publication Critical patent/JPH07107939A/en
Application granted granted Critical
Publication of JP2646421B2 publication Critical patent/JP2646421B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P60/00Technologies relating to agriculture, livestock or agroalimentary industries
    • Y02P60/80Food processing, e.g. use of renewable energies or variable speed drives in handling, conveying or stacking
    • Y02P60/87Re-use of by-products of food processing for fodder production

Landscapes

  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Fodder In General (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【0001】[0001]

【産業上の利用分野】本発明は油糧種子から得られる糖
脂質を有効成分とする肥満予防剤に関する。
BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a prophylactic agent for obesity containing glycolipids obtained from oilseed as an active ingredient.

【0002】[0002]

【従来の技術】大豆、菜種、ゴマ等の油糧種子から油脂
を製造するには、通常、該種子を圧搾し、および/また
はヘキサン等の有機溶剤で抽出して原油を得、これを貯
蔵タンクで静置して沈澱物いわゆるオリを析出させ、も
しくは水や水蒸気を吹き込んでガム質を水和、凝集さ
せ、これらを分離後、必要に応じて脱酸、脱色、脱臭等
の精製処理を施して油脂製品となしている。
2. Description of the Related Art In order to produce oils and fats from oil seeds such as soybeans, rapeseed, sesame, etc., usually, the seeds are squeezed and / or extracted with an organic solvent such as hexane to obtain crude oil, which is stored. Leave it in a tank to precipitate a precipitate, or so-called ori, or blow water or steam to hydrate and agglomerate the gum.After separating them, purify, if necessary, deacidification, decolorization, deodorization, etc. The product is treated as an oil and fat product.

【0003】ここで、ガム質は油滓ともよばれ、一般に
水分50〜80重量%、油分20〜50重量%からな
り、このうち油分はトリグリセリドを主成分とする中性
脂質、脂肪酸のほか、レシチンと通称されるリン脂質お
よび糖脂質を含む。かかるガム質は水分を除去してペー
スト状のレシチンとし、さらにはこれをアセトン、エタ
ノール等の溶剤を用いてレシチンを濃縮したり、その個
々の成分すなわちホスファチジルコリン、ホスファチジ
ルエタノールアミン、ホスファチジルイノシトール等を
高純度に精製し、食品、化粧品、農薬、医薬品等の分野
における乳化剤として利用されている。また、この際に
分離されたグリセリドや脂肪酸も油脂関連製品に再利用
されている。しかしながら、ステリルグリコシドおよび
アシル化ステリルグリコシド等の糖脂質を主体とする成
分は未だに産業的な利用法、用途が見出されておらず、
有効活用されるに至っていない。
[0003] Here, the gum substance is also called a soapstock, and generally comprises 50 to 80% by weight of water and 20 to 50% by weight of an oil component. Among these, the oil component includes neutral lipids and fatty acids containing triglyceride as a main component and lecithin. And phospholipids and glycolipids commonly referred to as Such gums are removed from water to form a paste-like lecithin, which is then concentrated using a solvent such as acetone or ethanol, or the individual components thereof such as phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, etc. are highly concentrated. It is purified to a high degree of purity and used as an emulsifier in the fields of food, cosmetics, agricultural chemicals, pharmaceuticals and the like. In addition, the glycerides and fatty acids separated at this time are also reused in oil and fat related products. However, components based on glycolipids such as steryl glycosides and acylated steryl glycosides have not yet been found for industrial use or use.
It has not been used effectively.

【0004】一方、原油を静置すると析出してくる沈澱
物であるオリは、例えばゴマ油の製造工程では、通常、
ゴマ油から分離され、廃棄処分されている。なおこのオ
リ中にはステリルグリコシドおよびそのアシル化物を主
体とする糖脂質が含有されていることが知られている。
[0004] On the other hand, in the process of producing sesame oil, for example, ori, which is a precipitate that precipitates when crude oil is allowed to stand, is usually used.
Separated from sesame oil and disposed of. It is known that the ori contains glycolipids mainly containing steryl glycosides and acylated products thereof.

【0005】ところで、生物における肥満現象は、遺伝
的あるいは病的なものを除けば、一般に摂取カロリーの
過剰によってもたらされ、体脂肪が蓄積し、その外見の
特異性のみならず種々の疫病をひき起こす原因ともなる
ことが懸念されている。例えばGordonら、 Ann. Inter
n. Med., 第87巻、第393〜397頁、1977年
によれば、肥満により糖尿病や心臓病を誘発することが
示唆されている。このため肥満を治療することはもとよ
り、未然に防止する観点からも種々の研究開発が進めら
れているが、殊に肥満予防の面からは未だ有効な対策、
手法が見出されていないのが現状である。
[0005] By the way, the obesity phenomenon in organisms is generally caused by excess calorie intake, except for genetic or pathological ones, and accumulates body fat, causing not only the specificity of its appearance but also various plagues. It is feared that it may cause it. For example, Gordon et al., Ann. Inter
According to n. Med., 87, 393-397, 1977, it is suggested that obesity induces diabetes and heart disease. For this reason, various research and development have been promoted not only to treat obesity but also to prevent it in advance, but still effective measures, especially from the aspect of obesity prevention,
At present, no method has been found.

【0006】すなわち、肥満予防の従来の方法はその大
半が摂取カロリーを限定する食事制限によるものである
が、これには精神的困難さを伴い実行しがたく、またこ
れが過度になれば栄養障害を引き起こしたり、あるいは
拒食症といった病的症状を呈する危険性がある。また、
薬剤投与による肥満防止もあるが、効能とともに副作用
を考慮しなければならず、肥満の予防のために個人レベ
ルにおいて安易かつ簡便に使用できる方法とはいいがた
い。
[0006] That is, most of the conventional methods for preventing obesity are based on dietary restrictions that limit the calorie intake, but this is accompanied by mental difficulty and is difficult to carry out. Or risk of pathological symptoms such as anorexia nervosa. Also,
Although obesity can be prevented by drug administration, side effects as well as efficacy must be taken into consideration, and it is difficult to say that a method that can be used easily and simply at the individual level to prevent obesity is used.

【0007】[0007]

【発明が解決しようとする課題】したがって本発明の目
的は、汎用的な油糧種子の成分を利用した、食事制限を
伴わず、副作用の懸念のない、かつ簡便に使用できる肥
満予防剤を提供することにある。
SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to provide a prophylactic agent for obesity which utilizes general-purpose oilseed components, does not involve dietary restrictions, has no concern about side effects, and can be used easily. Is to do.

【0008】[0008]

【課題を解決するための手段】前記目的に対し、本発明
者らは、油糧種子中の種々の成分と肥満予防効果との関
連性について鋭意検討し、本発明を完成するに至った。
すなわち本発明は、油糧種子から油脂を製造する工程で
発生するガム質またはオリを低級アルコールで分画して
得られる、糖脂質を有効成分とする肥満予防剤である。
Means for Solving the Problems With respect to the above object, the present inventors have intensively studied the relationship between various components in oilseed and the effect of preventing obesity, and have completed the present invention.
That is, the present invention is an anti-obesity agent comprising a glycolipid as an active ingredient, which is obtained by fractionating gum or odor generated in a step of producing an oil or fat from oil seeds with a lower alcohol.

【0009】本発明の出発原料として用いる油糧種子
は、大豆、菜種、トウモロコシ、ゴマ、綿実、ひまわ
り、紅花、亜麻、パーム等の汎用的な油脂生産用原料で
あり、とりわけ大豆、ゴマが好ましい。かかる油糧種子
を焙煎処理の有無にかかわらず、圧搾および/または溶
剤抽出して原油を製造し、これを例えば20〜50℃で
2〜10日間静置するとオリが沈澱してくる。あるいは
前記原油に対して水あるいは水蒸気を1〜10重量%吹
き込むとガム質が凝集、沈澱する。ついで本発明では、
かかるガム質またはオリから本発明における有効成分を
分画、濃縮する。
The oilseed used as a starting material in the present invention is a general-purpose raw material for producing oils and fats such as soybeans, rapeseed, corn, sesame, cottonseed, sunflower, safflower, flax, and palm. preferable. Regardless of whether or not the oil seed is roasted, squeezing and / or solvent extraction is performed to produce a crude oil, which is allowed to stand at, for example, 20 to 50 ° C. for 2 to 10 days, and deposits are formed. Alternatively, when water or steam is blown into the crude oil in an amount of 1 to 10% by weight, the gums coagulate and precipitate. Then, in the present invention,
The active ingredient in the present invention is fractionated and concentrated from the gum substance or the waste.

【0010】前記ガム質を用いる場合は、まずこれから
適当な乾燥手段を用いて水分を除き、さらにアセトン等
のケトン系有機溶剤にトリグリセリド、ジグリセリド等
のグリセリドからなる中性脂質、脂肪酸、着色物質、有
臭成分等を溶解させ分離し、不溶物としてレシチン主体
の極性脂質の沈澱物を得る。この沈澱物にはホスファチ
ジルコリン、ホスファチジルエタノールアミン、ホスフ
ァチジルイノシトール、ホスファチジルセリン、ホスフ
ァチジン酸、それらのリゾ体等のリン脂質からなるレシ
チン分のほか、本発明に係わる糖脂質が含有されてい
る。
In the case of using the gum substance, first, water is removed therefrom using a suitable drying means, and neutral lipids, fatty acids, coloring substances and glycerides such as triglyceride and diglyceride are added to a ketone organic solvent such as acetone. The odorous components and the like are dissolved and separated to obtain a precipitate of polar lipids mainly comprising lecithin as insolubles. The precipitate contains lecithin composed of phospholipids such as phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, phosphatidic acid, and lyso-form thereof, and the glycolipid according to the present invention.

【0011】次に、前記極性脂質の乾燥物を、例えばヘ
キサンに溶解してシリカゲルカラム(Wako gel C-100)
に供し、ヘキサンを溶出溶剤としてまずレシチン成分を
溶出させ、ついでメタノールあるいはエタノール等の低
級アルコールを溶出溶剤として糖脂質成分を溶出させ
る。ここに得られる糖脂質分画物は、シトステロール、
カンペステロール、スティグマステロール等の油糧種子
由来のステロール類と、グルコース、ガラクトース、ス
タキオース、ラフィノース等の油糧種子由来の糖類とが
結合したステリルグリコシド、およびそのアシル化物す
なわち糖鎖の6位の水酸基とパルミチン酸、オレイン
酸、リノール酸等とがエステル結合したものを主成分と
して含む。なお要すれば、前記糖脂質分画物を新たな前
記低級アルコールに溶解し、再度同様のシリカゲルカラ
ムクロマトグラフィーに供することにより、アシル化ス
テリルグリコシドがさらに濃縮された区分、および遊離
ステリルグリコシドがより一層濃縮された区分に分ける
ことができる。
Next, the dried product of the polar lipid is dissolved in, for example, hexane to obtain a silica gel column (Wako gel C-100).
First, the lecithin component is eluted using hexane as an eluting solvent, and then the glycolipid component is eluted using a lower alcohol such as methanol or ethanol as an eluting solvent. The glycolipid fraction obtained here is sitosterol,
Campesterol, oilseeds such as stigmasterol
Derived sterols and saccharides derived from oilseed such as glucose, galactose, stachyose, raffinose and the like, and acylated products thereof, that is, the hydroxyl group at the 6-position of the sugar chain and palmitic acid, oleic acid, and linoleic acid And the like as the main component. If necessary, the glycolipid fraction was dissolved in the new lower alcohol, and subjected to the same silica gel column chromatography again, whereby the acylated steryl glycoside was further concentrated, and the free steryl glycoside was further concentrated. Can be further divided into more concentrated sections.

【0012】また前記オリを使用する場合は、これを例
えばヘキサンに分散させて中性脂質等を除いたヘキサン
不溶区分を分取した後、さらに低級アルコールに分散さ
せ可溶区分を得、あるいはヘキサン/低級アルコール=
1/9〜9/1に分散ないし溶解させ分別して低級アル
コール可溶区分を得、もしくは低級アルコールに分散さ
せ可溶区分を得、これらのいずれかより低級アルコール
を除去して糖脂質を主成分とする分画物を得ることがで
きる。ここに、低級アルコールとしては溶解性の点から
メタノールまたはエタノールが好ましく、また要すれば
前記分別操作を40〜50℃に加温し、その後冷却する
ことにより分画効率を高めることができる。
When using the above-mentioned orifice, it is dispersed in, for example, hexane to separate a hexane-insoluble fraction from which neutral lipids and the like have been removed, and then dispersed in a lower alcohol to obtain a soluble fraction. / Lower alcohol =
Disperse or dissolve in 1/9 to 9/1 and fractionate to obtain a soluble fraction of lower alcohol, or disperse in lower alcohol to obtain a soluble fraction, and remove lower alcohol from any of these to make glycolipid the main component. Can be obtained. Here, the lower alcohol is preferably methanol or ethanol from the viewpoint of solubility, and if necessary, the fractionation operation can be heated to 40 to 50 ° C. and then cooled to increase the fractionation efficiency.

【0013】かくして得られる糖脂質分画物は、前記の
低級アルコールを用いる溶剤分別を繰り返すか、または
ガム質を用いる場合と同様に、これを低級アルコールに
溶解しシリカゲルカラムクロマトグラフィーに供するこ
とにより、他のオリ成分と遊離ステリルグリコシド濃縮
区分とに分離することができる。
The glycolipid fraction thus obtained is obtained by repeating the above-mentioned solvent separation using a lower alcohol, or dissolving it in a lower alcohol and subjecting it to silica gel column chromatography as in the case of using gum. , Other ori components and free steryl glycoside enriched fractions.

【0014】本発明では、上述のようにして分画した糖
脂質を有効成分とする肥満予防剤が開発される。すなわ
ちステリルグリコシドおよび/またはそのアシル化物を
少なくとも0.1重量%以上含有する糖脂質分画物、あ
るいは各々の糖脂質の濃縮物を、単独で、または公知の
食品用素材に添加して飲食物となし、また飼料用原料に
配合して動物用飼料とし、もしくは医薬用に適する成
分、担体等とともに医薬製剤とする。ここで、配合する
分画物中の糖脂質成分が0.1重量%未満であると、本
発明の目的とする肥満予防効果を発揮させるために多量
の分画物を配合しなければならず、またその際に混在す
るその他の成分が本発明の効果を抑制するおそれもあ
る。
In the present invention, an obesity preventive agent comprising the glycolipid fractionated as described above as an active ingredient is developed. That is, a glycolipid fraction containing at least 0.1% by weight or more of steryl glycoside and / or an acylated product thereof, or a concentrate of each glycolipid alone or added to a known food material is used for eating and drinking. It can be used as an animal feed or as a pharmaceutical preparation together with ingredients and carriers suitable for pharmaceutical use. Here, when the glycolipid component in the fraction to be blended is less than 0.1% by weight, a large amount of the fraction must be blended in order to exert the obesity prevention effect aimed at by the present invention. In addition, other components mixed at that time may suppress the effect of the present invention.

【0015】本発明の肥満予防剤は、飲食物や動物用飼
料にあっては、糖脂質を含有する分画物または各糖脂質
の濃縮物を、概ね0.5〜10重量%、かつステリルグ
リコシドおよび/またはアシル化物を0.05〜5重量
%程度配合すれば十分に効果を奏する。また医薬製剤と
しては、公知の結合剤、賦形剤等を添加し、常法により
粉末剤、粒剤、錠剤またはカプセル剤となして経口的に
服用でき、あるいは常用の安定化剤、助剤等ととも注射
剤となし非経口的に投与することもできる。この場合の
本発明に係わる糖脂質含有分画物または濃縮物の配合量
は、約0.1〜50重量%であり、かつステリルグリコ
シドおよび/またはそのアシル化物として0.1〜10
重量%程度である。またその投与量は、症状により適宜
に変更できるが、ほぼ10〜100mg/kg/日である。
The agent for preventing obesity according to the present invention is preferably used in foods and drinks and animal feeds in a fraction containing glycolipids or a concentrate of each glycolipid in an amount of about 0.5 to 10% by weight, and A sufficient effect can be obtained by adding about 0.05 to 5% by weight of the lyl glycoside and / or acylated product. As a pharmaceutical preparation, known binders, excipients, and the like can be added orally in the form of powders, granules, tablets or capsules by ordinary methods, or can be taken orally, or can be used as usual stabilizers and auxiliaries. It can also be administered parenterally without injections. In this case, the blending amount of the glycolipid-containing fraction or concentrate according to the present invention is about 0.1 to 50% by weight, and 0.1 to 10% by weight of steryl glycoside and / or its acylated product.
% By weight. The dose can be appropriately changed depending on the condition, but is about 10 to 100 mg / kg / day.

【0016】[0016]

【実施例】以下の参考例および実施例において%は重量
基準である。 〔参考例1 大豆レシチンおよび糖脂質各分画物の調
製〕大豆をヘキサン抽出して得た原油の脱ガム工程で発
生するガム質を乾燥し、この乾燥物1kgに10倍容量の
アセトンを加え、攪拌後、沈澱物を集め、減圧下にアセ
トンを留去してアセトン不溶物800gを得た。つい
で、このアセトン不溶物600gをヘキサン7リットル
に溶解してシリカゲルカラム(Wako gel C-100、1.2
kg)に供し、ヘキサン2リットルを流して溶出区分を集
め、溶剤を減圧留去してレシチン分画物F1とした。さ
らにエタノール10リットルを流して溶出区分を集め、
溶剤を減圧留去し糖脂質分画物F2とした。F1および
F2の収量は、それぞれ540gおよび55gであっ
た。またF1の組成を高速液体クロマトグラフィーで分
析したところ、ホスファチジルコリン30%、ホスファ
チジルエタノールアミン26%およびホスファチジルイ
ノシトール16%を主な成分とするものであり、F2の
組成を高速液体クロマトグラフィーで分析した結果、ス
テリルグリコシド14%、アシル化ステリルグリコシド
40%、その他46%であった。
EXAMPLES In the following Reference Examples and Examples,% is based on weight. [Reference Example 1 Preparation of soybean lecithin and glycolipid fractions] The gum generated in the degumming step of crude oil obtained by extracting hexane from soybeans was dried, and 10 kg of acetone was added to 1 kg of the dried product. After stirring, the precipitate was collected and acetone was distilled off under reduced pressure to obtain 800 g of acetone-insoluble matter. Then, 600 g of this acetone-insoluble matter was dissolved in 7 liters of hexane, and the mixture was dissolved in a silica gel column (Wako gel C-100, 1.2 g).
kg), and 2 liters of hexane was flowed to collect elution fractions, and the solvent was distilled off under reduced pressure to obtain a lecithin fraction F1. Further flow 10 liters of ethanol to collect the elution fraction,
The solvent was distilled off under reduced pressure to obtain glycolipid fraction F2. The yields of F1 and F2 were 540 g and 55 g, respectively. When the composition of F1 was analyzed by high performance liquid chromatography, it was found that 30% of phosphatidylcholine, 26% of phosphatidylethanolamine and 16% of phosphatidylinositol were the main components, and the composition of F2 was analyzed by high performance liquid chromatography. , Steryl glycoside 14%, acylated steryl glycoside 40%, and other 46%.

【0017】F1の500gを10倍容量のエタノール
に分散させ、エタノール可溶区分とエタノール不溶区分
とに分画した。溶剤を留去した後の収量は、エタノール
可溶区分(F1−1):150g、エタノール不溶区分
(F1−2):350gであり、各々の組成を分析した
ところ、F1−1はホスファチジルエタノールアミン2
6%およびホスファチジルイノシトール28%を主成分
とするレシチン濃縮物であり、F1−2はホスファチジ
ルコリン57%を主成分とするレシチン濃縮物であっ
た。
500 g of F1 was dispersed in 10 volumes of ethanol and fractionated into an ethanol-soluble section and an ethanol-insoluble section. The yield after distilling off the solvent was 150 g of the ethanol-soluble fraction (F1-1) and 350 g of the ethanol-insoluble fraction (F1-2). When the respective compositions were analyzed, F1-1 was found to be phosphatidylethanolamine. 2
F1-2 was a lecithin concentrate containing 6% and phosphatidylinositol as a main component, and F1-2 was a lecithin concentrate containing phosphatidylcholine as a main component at 57%.

【0018】一方、前記F2の50gをエタノール50
0mlに溶解してシリカゲルカラム(Wako gel C-100、1
kg)に供し、エタノールを流して最初の溶出区分2リッ
トル(F2−1)、続く溶出区分2リットル(F2−
2)、さらに続く溶出区分2リットル(F2−3)を分
取した。各区分から溶剤を留去し、その収量を求め、組
成分析を行ったところ、F2−1は収量30g、アシル
化ステリルグリコシド88%を主成分とする糖脂質濃縮
物であり、F2−3は収量18g、遊離ステリルグリコ
シド92%を主成分とする糖脂質濃縮物であった。
On the other hand, 50 g of the above F2 was
0 ml and dissolved in a silica gel column (Wako gel C-100, 1
kg), and flowed with ethanol, and then 2 liters of the first elution section (F2-1) and 2 liters of the subsequent elution section (F2-
2) Then, 2 liters (F2-3) of the subsequent elution fraction were collected. The solvent was distilled off from each section, the yield was determined, and composition analysis was performed. As a result, F2-1 was a glycolipid concentrate having a yield of 30 g and an acylated steryl glycoside of 88% as a main component. The yield was 18 g, which was a glycolipid concentrate containing 92% of free steryl glycoside as a main component.

【0019】〔実施例1〕4週令のSD系雄性ラット7
匹を1群とし、大豆油10%を含む大豆油添加区を対照
群、この大豆油5%を以下に示す同量の他成分に置き換
え、それぞれ試験群とした。レシチン分画物添加区:参
考例1に記載のレシチン分画物F1、糖脂質分画物添加
区:参考例1に記載の糖脂質分画物F2、レシチン濃縮
物(1)添加区:参考例1に記載のエタノール可溶区分
F1−1、レシチン濃縮物(2)添加区:参考例1に記
載のエタノール不溶区分F1−2。各試験区の飼料組成
を表1に示す。
[Example 1] Male SD rats 7 weeks old 4 weeks old
The animals were grouped as one group, a soybean oil-added group containing 10% soybean oil was replaced with a control group, and 5% of this soybean oil was replaced with the same amount of the other components shown below, and each group was a test group. Lecithin fraction added section: Lecithin fraction F1 described in Reference Example 1, glycolipid fraction added section: Glycolipid fraction F2 described in Reference Example 1, lecithin concentrate (1) added section: Reference Ethanol-soluble section F1-1 described in Example 1, lecithin concentrate (2) added section: ethanol-insoluble section F1-2 described in Reference Example 1. Table 1 shows the feed composition of each test plot.

【0020】[0020]

【表1】 注 1)ビタミンミックスおよびミネラルミックス:日
本クレア(株)製、AIN−76 2)〜5):参考例1参照
[Table 1] Note 1) Vitamin mix and mineral mix: AIN-762 manufactured by CLEA Japan, Inc. 2) to 5): Refer to Reference Example 1.

【0021】水と飼料を自由に摂取させて3週間飼育試
験を行い、試験終了後、各群ラットの体重増加量、飼料
摂取量、飼料効率を算出し、糞の排泄量の測定とともに
糞中の総脂質量および総コレステロール量を常法により
分析し、また解剖して副睾丸周囲脂肪組織および肝臓組
織の重量を測定した。その結果を表2、表3および表4
に示す。糖脂質分画物添加区では、大豆油のみの区やレ
シチン添加区に比べ、飼料の摂取量が多いにもかかわら
ず体重増加が少なく、飼料効率は低い値を示した(表
2)。排泄された糞重量が多く、糞中へ排泄される脂質
およびコレステロールの量も他の区に比べて多かった
(表3)。また副睾丸周囲脂肪組織および肝臓組織の重
量も有意に小さかった(表4)。これらの結果から、ス
テリルグリコシドおよびそのアシル化物を含む糖脂質分
画物の配合により体脂肪の蓄積が抑制され、肥満を予防
できることが明らかになった。
A three-week breeding test was conducted by freely ingesting water and feed. After the test was completed, the body weight gain, feed intake, and feed efficiency of each group of rats were calculated. The total lipid content and total cholesterol content were analyzed by a conventional method, and dissected to measure the weight of epididymal adipose tissue and liver tissue. Tables 2, 3 and 4 show the results.
Shown in In the glycolipid fraction-added group, the body weight gain was small and the feed efficiency was low in spite of the large intake of feed, compared to the group containing only soybean oil and the group added with lecithin (Table 2). The weight of the excreted feces was large, and the amounts of lipids and cholesterol excreted in the feces were larger than those in the other groups (Table 3). The weight of the epididymal adipose tissue and liver tissue was also significantly smaller (Table 4). From these results, it was clarified that the addition of a glycolipid fraction containing steryl glycoside and an acylated product thereof suppresses the accumulation of body fat and can prevent obesity.

【0022】[0022]

【表2】 注)各値は平均値±標準誤差で示した。また記号の異な
る試験区間は危険率5%以下で有意差がある。
[Table 2] Note) Each value is shown as the mean ± standard error. Test sections with different symbols have a significant difference with a risk rate of 5% or less.

【0023】[0023]

【表3】 [Table 3]

【0024】[0024]

【表4】 [Table 4]

【0025】〔参考例2 ゴマ糖脂質分画物および濃縮
物の調製〕ゴマ種子を常法により焙煎、圧搾して得た原
油を貯蔵タンクにて40〜25℃で10日間静置し、析
出した沈澱物(オリ)を濾別した後、この10kgを50
〜60℃のエタノール50リットルで3回繰り返し洗浄
した。油脂分および不溶物を除去し、集めたエタノール
層から減圧でエタノールを留去し、固形分800gを得
た。これをヘキサン5リットルに溶解し、参考例1の記
載と同様にシリカゲルカラム(Wako gel C-100)に供し
て、ヘキサン2リットルを流下させたときの溶出区分
(レシチン分画物)、さらにエタノール15リットルを
流下させたときの溶出区分(糖脂質分画物、F3)に分
けた。F3は、収量600gで、高速液体クロマトグラ
フィーによる組成分析の結果、ステリルグリコシド85
%、アシル化ステリルグリコシド5%、1,28−オク
タコサ二酸8%、その他2%であった。
Reference Example 2 Preparation of Sesame Glycolipid Fraction and Concentrate Crude oil obtained by roasting and pressing sesame seeds by a conventional method was allowed to stand in a storage tank at 40 to 25 ° C. for 10 days. After filtering out the deposited precipitate (ori), 10 kg of this
Washing was repeated three times with 50 liters of ethanol at 6060 ° C. Oil and fats and insolubles were removed, and ethanol was distilled off from the collected ethanol layer under reduced pressure to obtain 800 g of solids. This was dissolved in 5 liters of hexane, applied to a silica gel column (Wako gel C-100) in the same manner as described in Reference Example 1, and eluted with 2 liters of hexane (lecithin fraction), and further ethanol. It was divided into elution categories (glycolipid fraction, F3) when flowing down 15 liters. F3 was obtained in a yield of 600 g. As a result of composition analysis by high performance liquid chromatography, steryl glycoside 85 was obtained.
%, Acylated steryl glycoside 5%, 1,28-octacosadioic acid 8%, and other 2%.

【0026】ついでF3の500gをエタノール5リッ
トルに溶解して同様のシリカゲルカラムに供し、エタノ
ールを流下させ、溶出区分を2リットルずつ3区分(F
3−1、F3−2およびF3−3)として分取した。各
区分から溶剤を留去し、その収量を測定するとともに組
成分析したところ、F3−1は収量4g、アシル化ステ
リルグリコシド93%を主成分とする糖脂質濃縮物であ
り、F3−3は収量441g、遊離ステリルグリコシド
95%の糖脂質濃縮物であった。
Next, 500 g of F3 was dissolved in 5 liters of ethanol and applied to the same silica gel column, and the ethanol was allowed to flow down.
3-1 and F3-2 and F3-3). The solvent was distilled off from each section, the yield was measured, and the composition was analyzed. F3-1 was a 4 g yield, a glycolipid concentrate mainly containing 93% of acylated steryl glycoside, and F3-3 was a yield. 441 g, a glycolipid concentrate of 95% free steryl glycoside.

【0027】〔実施例2〕4週令のSD系雄性ラット7
匹を1群とした。飼料組成は、表1に記載の実施例1で
使用した大豆油添加区を対照群とし、この大豆油1%を
以下に示す同量の他成分に置き換え、それぞれを試験群
とした。糖脂質分画物添加区:参考例2に記載の糖脂質
分画物F3、糖脂質濃縮物(1)添加区:参考例2に記
載のアシル化ステリルグリコシドを主成分とするF3−
1、糖脂質濃縮物(2)添加区:参考例2に記載のステ
リルグリコシドを主成分とするF3−3。
[Example 2] SD male rats of 4 weeks of age 7
The animals were grouped as one group. In the feed composition, the soybean oil-added group used in Example 1 shown in Table 1 was used as a control group, and 1% of this soybean oil was replaced with the same amount of other components shown below, and each was used as a test group. Glycolipid fraction addition section: glycolipid fraction F3 described in Reference Example 2, glycolipid concentrate (1) addition section: F3- containing acylated steryl glycoside described in Reference Example 2 as a main component
1. Glycolipid concentrate (2) added section: F3-3 containing steryl glycoside as described in Reference Example 2 as a main component.

【0028】実施例1と同様に水と飼料を自由摂取させ
3週間飼育試験し、各群のラットの体重増加量、飼料摂
取量および飼料効率を求め、また肝臓および脂肪組織の
重量を測定した。その結果を表5および表6に示す。糖
脂質分画物および濃縮物を飼料中に添加すると、表5か
ら体重増加が抑制され、飼料効率が低いこと、また表6
から肝臓組織および皮下脂肪組織重量が小さいことが認
められ、肥満の予防に効果があることが明らかになっ
た。
In the same manner as in Example 1, water and feed were freely ingested and a three-week rearing test was carried out to determine the weight gain, feed intake and feed efficiency of the rats in each group, and the weight of liver and adipose tissue was measured. . The results are shown in Tables 5 and 6. Table 5 shows that when the glycolipid fraction and the concentrate were added to the feed, weight gain was suppressed and the feed efficiency was low.
From the results, it was confirmed that the weight of liver tissue and subcutaneous fat tissue was small, and it was clarified that it was effective in preventing obesity.

【0029】[0029]

【表5】 注)各値は平均値±標準誤差で示した。また記号の異な
る試験区間は危険率5%以下で有意差がある。 1)飼料組成は表1の大豆油添加区と同じ 2)参考例2の糖脂質分画物F3を1%添加 3)参考例2の糖脂質濃縮物F3−1を1%添加 4)参考例2の糖脂質濃縮物F3−3を1%添加
[Table 5] Note) Each value is shown as the mean ± standard error. Test sections with different symbols have a significant difference with a risk rate of 5% or less. 1) The feed composition is the same as the soybean oil-added group in Table 1 2) 1% of glycolipid fraction F3 of Reference Example 2 is added 3) 1% of glycolipid concentrate F3-1 of Reference Example 2 is added 4) Reference 1% of the glycolipid concentrate F3-3 of Example 2 was added.

【0030】[0030]

【表6】 [Table 6]

【0031】[0031]

【発明の効果】本発明によれば、大豆、ゴマ等の汎用的
な油糧種子から油脂を製造する工程で発生するガム質ま
たはオリを、メタノール、エタノール等の低級アルコー
ルで分画して得られるステリルグリコシドおよび/また
はそのアシル化物を含有する糖脂質分画物、またはそれ
らの濃縮物を有効成分とする肥満予防剤が提供される。
この肥満予防剤は、単独で使用でき、あるいは公知の原
材料に配合して飲食物、動物用飼料もしくは医薬製剤と
なすことができ、食事制限を必要とすることなく、また
副作用の懸念もなく、簡便に使用できる。
According to the present invention, gum or odor generated in the process of producing oils and fats from general-purpose oil seeds such as soybeans and sesame is obtained by fractionating with a lower alcohol such as methanol or ethanol. And a glycolipid fraction containing the steryl glycoside and / or an acylated product thereof, or a concentrate thereof, as an active ingredient.
This anti-obesity agent can be used alone, or can be used as a food or drink, an animal feed or a pharmaceutical formulation by mixing with known raw materials, without requiring dietary restrictions, and without the risk of side effects, Easy to use.

Claims (4)

(57)【特許請求の範囲】(57) [Claims] 【請求項1】 油糧種子から油脂を製造する工程で発生
するガム質またはオリを、低級アルコールで分画して得
られる、油糧種子由来のステロール類と糖類とが結合し
たステリルグリコシドおよびそのアシル化物を主成分と
して含む糖脂質を有効成分とする肥満予防剤。
The present invention relates to a method wherein sterols derived from oil seeds and saccharides, which are obtained by fractionating gum or odor generated in a step of producing an oil or fat from oil seeds with a lower alcohol, are combined.
Steryl glycoside and its acylated product
An anti-obesity agent comprising a glycolipid containing as an active ingredient.
【請求項2】 油糧種子が大豆またはゴマである請求項
1に記載の肥満予防剤。
2. The agent for preventing obesity according to claim 1, wherein the oil seed is soybean or sesame.
【請求項3】 低級アルコールがメタノールまたはエタ
ノールである請求項1または2に記載の肥満予防剤。
3. The agent for preventing obesity according to claim 1, wherein the lower alcohol is methanol or ethanol.
【請求項4】 糖脂質が油糧種子由来のステロール類と
糖類とが結合したステリルグリコシドおよび/またはア
シル化ステリルグリコシドである請求項1〜3のいずれ
かに記載の肥満予防剤。
4. The method according to claim 1, wherein the glycolipid is a sterol derived from oilseed.
The agent for preventing obesity according to any one of claims 1 to 3, which is a steryl glycoside and / or an acylated steryl glycoside bound to a saccharide .
JP5278992A 1993-10-12 1993-10-12 Obesity prevention agent Expired - Fee Related JP2646421B2 (en)

Priority Applications (1)

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Application Number Priority Date Filing Date Title
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Publication Number Publication Date
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JP2646421B2 true JP2646421B2 (en) 1997-08-27

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3618857B2 (en) * 1995-10-02 2005-02-09 竹本油脂株式会社 Processed sesame seeds
DE19738927A1 (en) * 1997-09-05 1999-03-11 Krupp Ag Hoesch Krupp Assembly to distil an oil seed extract containing solvent has two modules
JP2001097983A (en) * 1999-09-27 2001-04-10 Oriza Yuka Kk Plant extract including sphingo lipid and its production
JP2008038011A (en) * 2006-08-04 2008-02-21 Bizen Chemical Co Ltd Method for producing highly pure phospholipid
JP2009023964A (en) * 2007-07-20 2009-02-05 Ogawa & Co Ltd Diet effect imparting agent, diet perfume composition, diet cosmetic and diet food and drink
JP5752359B2 (en) * 2010-02-25 2015-07-22 富士フイルム株式会社 Weight gain inhibiting composition and food containing the same
CN105708834A (en) * 2011-10-18 2016-06-29 株式会社爱茉莉太平洋 Sirt1 activator including syringaresinol
JP7133306B2 (en) * 2017-12-01 2022-09-08 国立大学法人九州大学 Acyl steryl glucoside, method for producing acyl steryl glucoside, composition, antioxidant, blood lipid-lowering agent, anti-obesity agent, anti-tumor agent, and prophylactic or therapeutic agent for atherosclerosis

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